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首页> 外文期刊>Biochemistry >ANALYSIS OF FLUOROMETHYL GROUP CHIRALITY ESTABLISHES A COMMON STEREOCHEMICAL COURSE FOR THE ENOLPYRUVYL TRANSFERS CATALYZED BY EPSP SYNTHASE AND UDP-GLCNAC ENOLPYRUVYL TRANSFERASE
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ANALYSIS OF FLUOROMETHYL GROUP CHIRALITY ESTABLISHES A COMMON STEREOCHEMICAL COURSE FOR THE ENOLPYRUVYL TRANSFERS CATALYZED BY EPSP SYNTHASE AND UDP-GLCNAC ENOLPYRUVYL TRANSFERASE

机译：EPSP合酶和UDP-GLCNAC烯丙基戊基转移酶催化的烯丙基戊基转移的常规立体化学过程中的氟甲基手性分析

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摘要

The stereochemistry of transient methyl group formation at C-3 of phosphoenolpyruvate (PEP) in the reaction catalyzed by 5-enolpyruvylshikimate 3-phosphate (EPSP) synthase has been examined using the pseudosubstrates, (E)- and (Z)-3-fluorophosphoenolpyruvate (FPEP). Kinetically stable, chiral [H-1,H-2]fluoromethyl analogs of the reaction tetrahedral intermediate were isolated and subjected to decomposition and stereochemical analysis. EPSP synthase was found to catalyze the 2-re face addition of solvent-derived hydrogen to C-3 of FPEP (corresponding to the 2-si face of PEP). Comparison of these data with our prior analogous work on the MurA reaction [Kim, D. H., Lees, W. J., & Walsh, C. T. (1995) J. Am. Chem. Sec. 117, 6380-6381] suggests that the two enolpyruvyl transferases share a common stereochemical course, further strengthening the mechanistic, structural, and evolutionary relationship between the two enzymes.
机译：已使用伪底物（E）-和（Z）-3-氟代磷酸烯醇式丙酮酸检测了在5-烯醇式丙酮酸shi草酸酯3-磷酸（EPSP）合酶催化的反应中磷酸烯醇式丙酮酸（PEP）在C-3处的瞬时甲基形成的立体化学。 （FPEP）。分离出反应稳定的四面体中间体的手性[H-1，H-2]氟甲基类似物，并进行分解和立体化学分析。发现EPSP合酶可催化将溶剂衍生的氢2面添加到FPEP的C-3中（对应于PEP的2 si面）。这些数据与我们先前关于MurA反应的类似工作的比较[Kim，D. H.，Lees，W. J.，＆Walsh，C. T.（1995）J. Am。化学秒117，6380-6381]表明两种烯丙基丙酮基转移酶具有共同的立体化学过程，从而进一步增强了两种酶之间的机理，结构和进化关系。

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